DE2264224C3 - Herstellung eines vernetzten Polystyrol-Emulsionspolymerisats und seine Verwendung zum Trüben von Kunststoffen auf Methacrylatbasis - Google Patents
Herstellung eines vernetzten Polystyrol-Emulsionspolymerisats und seine Verwendung zum Trüben von Kunststoffen auf MethacrylatbasisInfo
- Publication number
- DE2264224C3 DE2264224C3 DE2264224A DE2264224A DE2264224C3 DE 2264224 C3 DE2264224 C3 DE 2264224C3 DE 2264224 A DE2264224 A DE 2264224A DE 2264224 A DE2264224 A DE 2264224A DE 2264224 C3 DE2264224 C3 DE 2264224C3
- Authority
- DE
- Germany
- Prior art keywords
- styrene
- parts
- methyl methacrylate
- polystyrene
- emulsion polymer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000004793 Polystyrene Substances 0.000 title claims description 40
- 229920002223 polystyrene Polymers 0.000 title claims description 40
- 239000004908 Emulsion polymer Substances 0.000 title claims description 36
- 238000004519 manufacturing process Methods 0.000 title description 11
- 229920003023 plastic Polymers 0.000 title description 7
- 239000004033 plastic Substances 0.000 title description 7
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 title 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 63
- 239000002245 particle Substances 0.000 claims description 45
- 239000000178 monomer Substances 0.000 claims description 35
- 239000000203 mixture Substances 0.000 claims description 34
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 28
- 229920003229 poly(methyl methacrylate) Polymers 0.000 claims description 27
- 239000004926 polymethyl methacrylate Substances 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 21
- 238000006116 polymerization reaction Methods 0.000 claims description 20
- 229920000642 polymer Polymers 0.000 claims description 14
- 229920001577 copolymer Polymers 0.000 claims description 12
- 230000008569 process Effects 0.000 claims description 8
- 238000004132 cross linking Methods 0.000 claims description 6
- 239000000155 melt Substances 0.000 claims description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 4
- 239000003995 emulsifying agent Substances 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 238000010559 graft polymerization reaction Methods 0.000 claims description 2
- 229920001519 homopolymer Polymers 0.000 claims description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
- 239000012874 anionic emulsifier Substances 0.000 claims 2
- 239000004971 Cross linker Substances 0.000 claims 1
- 238000007720 emulsion polymerization reaction Methods 0.000 claims 1
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 21
- 239000006185 dispersion Substances 0.000 description 20
- 238000000465 moulding Methods 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 11
- 239000000839 emulsion Substances 0.000 description 11
- 239000008367 deionised water Substances 0.000 description 10
- 229910021641 deionized water Inorganic materials 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 9
- 238000000149 argon plasma sintering Methods 0.000 description 9
- 238000009826 distribution Methods 0.000 description 9
- 235000019395 ammonium persulphate Nutrition 0.000 description 8
- 238000001746 injection moulding Methods 0.000 description 8
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 7
- 230000005540 biological transmission Effects 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 238000001125 extrusion Methods 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 230000002776 aggregation Effects 0.000 description 3
- 239000012935 ammoniumperoxodisulfate Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 239000012188 paraffin wax Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- GUUVPOWQJOLRAS-UHFFFAOYSA-N Diphenyl disulfide Chemical compound C=1C=CC=CC=1SSC1=CC=CC=C1 GUUVPOWQJOLRAS-UHFFFAOYSA-N 0.000 description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 238000004220 aggregation Methods 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000015271 coagulation Effects 0.000 description 2
- 238000005345 coagulation Methods 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000004816 latex Substances 0.000 description 2
- 229920000126 latex Polymers 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- HSOOIVBINKDISP-UHFFFAOYSA-N 1-(2-methylprop-2-enoyloxy)butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(CCC)OC(=O)C(C)=C HSOOIVBINKDISP-UHFFFAOYSA-N 0.000 description 1
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 150000002019 disulfides Chemical class 0.000 description 1
- PVBRSNZAOAJRKO-UHFFFAOYSA-N ethyl 2-sulfanylacetate Chemical compound CCOC(=O)CS PVBRSNZAOAJRKO-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- YOZHLACIXDCHPV-UHFFFAOYSA-N n-(methoxymethyl)-2-methylprop-2-enamide Chemical compound COCNC(=O)C(C)=C YOZHLACIXDCHPV-UHFFFAOYSA-N 0.000 description 1
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 1
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 1
- 230000006855 networking Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- ZWWQICJTBOCQLA-UHFFFAOYSA-N o-propan-2-yl (propan-2-yloxycarbothioyldisulfanyl)methanethioate Chemical compound CC(C)OC(=S)SSC(=S)OC(C)C ZWWQICJTBOCQLA-UHFFFAOYSA-N 0.000 description 1
- 229920005787 opaque polymer Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 230000005501 phase interface Effects 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F257/00—Macromolecular compounds obtained by polymerising monomers on to polymers of aromatic monomers as defined in group C08F12/00
- C08F257/02—Macromolecular compounds obtained by polymerising monomers on to polymers of aromatic monomers as defined in group C08F12/00 on to polymers of styrene or alkyl-substituted styrenes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F285/00—Macromolecular compounds obtained by polymerising monomers on to preformed graft polymers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S525/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S525/902—Core-shell
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S525/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S525/932—Blend of matched optical properties
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Graft Or Block Polymers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2264224A DE2264224C3 (de) | 1972-12-30 | 1972-12-30 | Herstellung eines vernetzten Polystyrol-Emulsionspolymerisats und seine Verwendung zum Trüben von Kunststoffen auf Methacrylatbasis |
| FR7333382A FR2212345B1 (enrdf_load_stackoverflow) | 1972-12-30 | 1973-09-18 | |
| IT70180/73A IT999692B (it) | 1972-12-30 | 1973-10-26 | Procedimento per la preparazione di un polimero reticolato di stiro lo col processo in emulsione |
| JP14178573A JPS5731572B2 (enrdf_load_stackoverflow) | 1972-12-30 | 1973-12-17 | |
| NLAANVRAGE7317417,A NL181279C (nl) | 1972-12-30 | 1973-12-19 | Werkwijze voor de bereiding van troebele polymeren op methylmethacrylaat-basis, alsmede gevormd voortbrengsel, dat geheel of ten dele uit een dergelijk polymeer is vervaardigd. |
| CA188,629A CA1036740A (en) | 1972-12-30 | 1973-12-20 | Graft copolymers |
| US428011A US3914338A (en) | 1972-12-30 | 1973-12-26 | Opalescent methylmethacrylate polymer bodies |
| GB5981873A GB1428500A (en) | 1972-12-30 | 1973-12-27 | Graft copolymers |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2264224A DE2264224C3 (de) | 1972-12-30 | 1972-12-30 | Herstellung eines vernetzten Polystyrol-Emulsionspolymerisats und seine Verwendung zum Trüben von Kunststoffen auf Methacrylatbasis |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2264224A1 DE2264224A1 (de) | 1974-07-18 |
| DE2264224B2 DE2264224B2 (de) | 1981-01-15 |
| DE2264224C3 true DE2264224C3 (de) | 1981-11-19 |
Family
ID=5865815
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2264224A Expired DE2264224C3 (de) | 1972-12-30 | 1972-12-30 | Herstellung eines vernetzten Polystyrol-Emulsionspolymerisats und seine Verwendung zum Trüben von Kunststoffen auf Methacrylatbasis |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3914338A (enrdf_load_stackoverflow) |
| JP (1) | JPS5731572B2 (enrdf_load_stackoverflow) |
| CA (1) | CA1036740A (enrdf_load_stackoverflow) |
| DE (1) | DE2264224C3 (enrdf_load_stackoverflow) |
| FR (1) | FR2212345B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1428500A (enrdf_load_stackoverflow) |
| IT (1) | IT999692B (enrdf_load_stackoverflow) |
| NL (1) | NL181279C (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0122586B1 (de) * | 1983-04-16 | 1993-03-10 | Hoechst Aktiengesellschaft | Verfahren zur Hertellung von emulgator- und schutzkolloidfreie Emulsionspolymerisate. |
| US5621028A (en) * | 1992-05-16 | 1997-04-15 | Roehm Gmbh Chemische Fabrik | Light-scattering translucent polymethacrylate molded articles with good resistance to elevated temperature and weathering |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4108923A (en) * | 1974-07-05 | 1978-08-22 | The Goodyear Tire & Rubber Company | Poly(methyl methacrylate) composition |
| DE2722752C3 (de) * | 1977-05-20 | 1987-10-22 | Röhm GmbH, 6100 Darmstadt | Plastisole auf Basis von Methylmethacrylat-Mischpolymerisaten |
| GB2017121B (en) * | 1978-03-27 | 1982-08-18 | Labofina Sa | Process for preparing styrenic resins |
| US4264678A (en) * | 1979-05-29 | 1981-04-28 | Gaf Corporation | Core-shell polymers |
| US4391928A (en) * | 1981-09-04 | 1983-07-05 | Nl Industries, Inc. | Opacifying polymeric particle and uses |
| US5183851A (en) * | 1986-11-11 | 1993-02-02 | Elf Atochem Italia S.R.L. | Low haze transparent compositions and processes for preparing them |
| US5004785A (en) * | 1987-11-30 | 1991-04-02 | Mitsubishi Rayon Co., Ltd. | Light-diffusing methacrylic resin and process for production thereof |
| US4963624A (en) * | 1988-02-17 | 1990-10-16 | Mitsubishi Rayon Co., Ltd. | Process for producing light-diffusing methacrylic resin article |
| CA1303437C (en) * | 1988-02-29 | 1992-06-16 | Nobuo Kawahashi | Hollow polymer particles, process for production thereof, and use thereof as pigment |
| US5026782A (en) * | 1988-09-23 | 1991-06-25 | Union Oil Company Of California | Polymeric opaque particles and process for making same |
| US5053441A (en) * | 1988-09-23 | 1991-10-01 | Union Oil Company Of California | Core/shell particles and process for making same |
| US5147940A (en) * | 1988-09-23 | 1992-09-15 | Union Oil Company Of California | Polymeric opaque particles and process for making same |
| DE3907019A1 (de) * | 1989-03-04 | 1990-09-06 | Roehm Gmbh | Thermoplastisch verarbeitbare loesungsmittelbestaendige kunststoffmischungen |
| US5238992A (en) * | 1989-08-30 | 1993-08-24 | Edison Polymer Innovation Corporation | Microemulsion polymer blends |
| TW279871B (enrdf_load_stackoverflow) * | 1992-02-25 | 1996-07-01 | Takeda Pharm Industry Co Ltd | |
| WO1994024236A1 (en) * | 1993-04-21 | 1994-10-27 | Copytele, Inc. | Black and white electrophoretic particles and method of manufacture |
| US6355720B1 (en) | 2000-05-12 | 2002-03-12 | Johnson Polymer, Inc. | Latex formulations with reduced yellowing |
| EP1757638A1 (en) * | 2005-08-22 | 2007-02-28 | Rohm and Haas France SAS | Methods for using hollow sphere polymers |
| US9187580B2 (en) * | 2008-05-21 | 2015-11-17 | Sumitomo Seika Chemicals Co., Ltd. | Resin particle having many recesses on the surface thereof |
| JP6672166B2 (ja) | 2013-12-30 | 2020-03-25 | アベリス アーエス | 固体粒子状ビニル芳香族ポリマー組成物の調製用製造方法 |
| CN108329417B (zh) * | 2018-01-23 | 2020-05-12 | 五邑大学 | 纳米SiO2/有机硅改性核壳丙烯酸酯乳液及制备方法 |
| WO2024233076A1 (en) | 2023-05-09 | 2024-11-14 | Rohm And Haas Company | Architectural coating composition |
| WO2025096108A1 (en) | 2023-10-30 | 2025-05-08 | Rohm And Haas Company | Quick drying coating composition |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE496775A (enrdf_load_stackoverflow) * | 1949-07-05 | |||
| DE1123476B (de) * | 1953-09-08 | 1962-02-08 | Phil Oliver Wallis Burke Jun D | Verfahren zur Herstellung von unloeslichen, vernetzten Hochpolymeren kolloider Teilchengroesse |
| GB1039802A (en) * | 1963-01-25 | 1966-08-24 | Kanegafuchi Chemical Ind | A method of manufacturing vinylchloride-butadiene resin compositions |
| US3644249A (en) * | 1968-07-10 | 1972-02-22 | Mitsubishi Rayon Co | Polyvinyl chloride resin composition having excellent transparency, surface gloss and impact strength |
| GB1324190A (en) * | 1969-09-10 | 1973-07-18 | Sumitomo Chemical Co | Thermoplastic resinous material |
| US3781232A (en) * | 1970-08-25 | 1973-12-25 | Gaylord Research Institute | Graft copolymers having branches which are alternating copolymers,and processes therefor |
-
1972
- 1972-12-30 DE DE2264224A patent/DE2264224C3/de not_active Expired
-
1973
- 1973-09-18 FR FR7333382A patent/FR2212345B1/fr not_active Expired
- 1973-10-26 IT IT70180/73A patent/IT999692B/it active
- 1973-12-17 JP JP14178573A patent/JPS5731572B2/ja not_active Expired
- 1973-12-19 NL NLAANVRAGE7317417,A patent/NL181279C/xx not_active IP Right Cessation
- 1973-12-20 CA CA188,629A patent/CA1036740A/en not_active Expired
- 1973-12-26 US US428011A patent/US3914338A/en not_active Expired - Lifetime
- 1973-12-27 GB GB5981873A patent/GB1428500A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0122586B1 (de) * | 1983-04-16 | 1993-03-10 | Hoechst Aktiengesellschaft | Verfahren zur Hertellung von emulgator- und schutzkolloidfreie Emulsionspolymerisate. |
| US5621028A (en) * | 1992-05-16 | 1997-04-15 | Roehm Gmbh Chemische Fabrik | Light-scattering translucent polymethacrylate molded articles with good resistance to elevated temperature and weathering |
Also Published As
| Publication number | Publication date |
|---|---|
| NL181279C (nl) | 1987-07-16 |
| GB1428500A (en) | 1976-03-17 |
| NL7317417A (enrdf_load_stackoverflow) | 1974-07-02 |
| FR2212345B1 (enrdf_load_stackoverflow) | 1976-10-01 |
| JPS49109486A (enrdf_load_stackoverflow) | 1974-10-17 |
| NL181279B (nl) | 1987-02-16 |
| IT999692B (it) | 1976-03-10 |
| DE2264224A1 (de) | 1974-07-18 |
| US3914338A (en) | 1975-10-21 |
| DE2264224B2 (de) | 1981-01-15 |
| CA1036740A (en) | 1978-08-15 |
| JPS5731572B2 (enrdf_load_stackoverflow) | 1982-07-06 |
| FR2212345A1 (enrdf_load_stackoverflow) | 1974-07-26 |
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| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |